KR100645270B1 - Ｎ-(아미노-4,6-다이할로피리미딘)포름아미드의 제조 방법 - Google Patents
Ｎ-(아미노-4,6-다이할로피리미딘)포름아미드의 제조 방법 Download PDFInfo
- Publication number
- KR100645270B1 KR100645270B1 KR1019990059846A KR19990059846A KR100645270B1 KR 100645270 B1 KR100645270 B1 KR 100645270B1 KR 1019990059846 A KR1019990059846 A KR 1019990059846A KR 19990059846 A KR19990059846 A KR 19990059846A KR 100645270 B1 KR100645270 B1 KR 100645270B1
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- diamino
- dihalopyrimidine
- reaction
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims abstract description 24
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 14
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 12
- 235000019253 formic acid Nutrition 0.000 claims abstract description 12
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 239000000047 product Substances 0.000 claims description 12
- HWSJQFCTYLBBOF-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one Chemical compound NC1=NC(O)=C(N)C(O)=N1 HWSJQFCTYLBBOF-UHFFFAOYSA-N 0.000 claims description 10
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 8
- -1 quaternary ammonium halide Chemical class 0.000 claims description 7
- CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 150000008282 halocarbons Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 239000012467 final product Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 150000002430 hydrocarbons Chemical class 0.000 claims 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZXWGHENZKVQKPX-UHFFFAOYSA-N 4,6-dichloropyrimidine-2,5-diamine Chemical compound NC1=NC(Cl)=C(N)C(Cl)=N1 ZXWGHENZKVQKPX-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000003948 formamides Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NWWSFOPCCPZHAT-UHFFFAOYSA-N n-(5-amino-4,6-dichloropyrimidin-2-yl)formamide Chemical compound NC1=C(Cl)N=C(NC=O)N=C1Cl NWWSFOPCCPZHAT-UHFFFAOYSA-N 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- IIVYOQGIZSPVFZ-UHFFFAOYSA-N 2,5-diamino-4-hydroxy-1h-pyrimidin-6-one;hydrochloride Chemical compound Cl.NC1=NC(O)=C(N)C(=O)N1 IIVYOQGIZSPVFZ-UHFFFAOYSA-N 0.000 description 1
- SZYMVPCRVAQEHH-UHFFFAOYSA-N 4,6-dibromopyrimidine-2,5-diamine Chemical group NC1=NC(Br)=C(N)C(Br)=N1 SZYMVPCRVAQEHH-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- FLSVUQSDOOPGNL-UHFFFAOYSA-N n'-(2-amino-4,6-dichloropyrimidin-5-yl)-n,n-dimethylmethanimidamide Chemical compound CN(C)C=NC1=C(Cl)N=C(N)N=C1Cl FLSVUQSDOOPGNL-UHFFFAOYSA-N 0.000 description 1
- XYWHZUCZNRMJGO-UHFFFAOYSA-N n-(2-amino-4,6-dichloropyrimidin-5-yl)formamide Chemical compound NC1=NC(Cl)=C(NC=O)C(Cl)=N1 XYWHZUCZNRMJGO-UHFFFAOYSA-N 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- VTGOHKSTWXHQJK-UHFFFAOYSA-N pyrimidin-2-ol Chemical compound OC1=NC=CC=N1 VTGOHKSTWXHQJK-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/30—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Communicable Diseases (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98124188 | 1998-12-21 | ||
| EP98124188.8 | 1998-12-21 | ||
| EP99100788 | 1999-01-18 | ||
| EP99100788.1 | 1999-01-18 | ||
| EP99107161 | 1999-04-12 | ||
| EP99107161.4 | 1999-04-12 | ||
| US14610699P | 1999-07-29 | 1999-07-29 | |
| US60/146106 | 1999-07-29 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR20000052540A KR20000052540A (ko) | 2000-08-25 |
| KR100645270B1 true KR100645270B1 (ko) | 2006-11-13 |
Family
ID=27443679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019990059846A KR100645270B1 (ko) | 1998-12-21 | 1999-12-21 | Ｎ-(아미노-4,6-다이할로피리미딘)포름아미드의 제조 방법 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US6271376B1 (no) |
| EP (2) | EP1013647B1 (no) |
| JP (1) | JP3543709B2 (no) |
| KR (1) | KR100645270B1 (no) |
| CN (1) | CN1156449C (no) |
| AT (2) | ATE252087T1 (no) |
| CA (1) | CA2293011C (no) |
| CZ (2) | CZ296753B6 (no) |
| DE (2) | DE59903535D1 (no) |
| DK (1) | DK1013647T3 (no) |
| ES (2) | ES2204798T3 (no) |
| HU (1) | HUP9904608A3 (no) |
| NO (1) | NO313878B1 (no) |
| PL (1) | PL337354A1 (no) |
| PT (1) | PT1013647E (no) |
| SK (2) | SK283681B6 (no) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7208010B2 (en) * | 2000-10-16 | 2007-04-24 | Conor Medsystems, Inc. | Expandable medical device for delivery of beneficial agent |
| US6241762B1 (en) | 1998-03-30 | 2001-06-05 | Conor Medsystems, Inc. | Expandable medical device with ductile hinges |
| US7208011B2 (en) * | 2001-08-20 | 2007-04-24 | Conor Medsystems, Inc. | Implantable medical device with drug filled holes |
| GB2344550A (en) * | 1998-12-09 | 2000-06-14 | Ibm | Pad design for electronic package |
| CA2424305A1 (en) | 2000-10-16 | 2002-04-25 | Conor Medsystems, Inc. | Expandable medical device for delivery of beneficial agent |
| US20040204756A1 (en) * | 2004-02-11 | 2004-10-14 | Diaz Stephen Hunter | Absorbent article with improved liquid acquisition capacity |
| US20040249443A1 (en) * | 2001-08-20 | 2004-12-09 | Shanley John F. | Expandable medical device for treating cardiac arrhythmias |
| US7056338B2 (en) * | 2003-03-28 | 2006-06-06 | Conor Medsystems, Inc. | Therapeutic agent delivery device with controlled therapeutic agent release rates |
| DK1509256T3 (da) * | 2002-05-24 | 2009-11-23 | Angiotech Int Ag | Præparater og fremgangsmåde til coating af medicinske implantater |
| JP2006505365A (ja) * | 2002-11-08 | 2006-02-16 | コナー メドシステムズ， インコーポレイテッド | 虚血障害後の組織のダメージを抑制するための方法および装置 |
| WO2004043509A1 (en) * | 2002-11-08 | 2004-05-27 | Conor Medsystems, Inc. | Expandable medical device and method for treating chronic total occlusions with local delivery of an angiogenic factor |
| US20040142014A1 (en) * | 2002-11-08 | 2004-07-22 | Conor Medsystems, Inc. | Method and apparatus for reducing tissue damage after ischemic injury |
| FR2849030A1 (fr) * | 2002-12-20 | 2004-06-25 | Isochem Sa | Procede de preparation des n-(2-amino-4, 6-dihalogenopyrimidin-5-yl) formamides |
| US20040202692A1 (en) * | 2003-03-28 | 2004-10-14 | Conor Medsystems, Inc. | Implantable medical device and method for in situ selective modulation of agent delivery |
| US20050010170A1 (en) * | 2004-02-11 | 2005-01-13 | Shanley John F | Implantable medical device with beneficial agent concentration gradient |
| EP1610823B1 (en) | 2003-03-28 | 2011-09-28 | Innovational Holdings, LLC | Implantable medical device with continuous agent concentration gradient |
| JPWO2004103979A1 (ja) * | 2003-05-26 | 2006-07-20 | 住友化学株式会社 | Ｎ−（２−アミノ−４，６−ジクロロピリミジン−５−イル）ホルムアミドの製造方法 |
| US7208596B2 (en) * | 2003-11-25 | 2007-04-24 | Bristol-Myers Squibb Pharma Company | Processes for the preparation of pyrazolo[1,5-a]-1,3,5-triazines and intermediates thereof |
| US20050287287A1 (en) * | 2004-06-24 | 2005-12-29 | Parker Theodore L | Methods and systems for loading an implantable medical device with beneficial agent |
| CN101003511B (zh) * | 2007-01-19 | 2010-06-09 | 中国科学院上海有机化学研究所 | 制备2-氨基-4,6-二氯-5-甲酰氨基嘧啶的方法 |
| CZ305457B6 (cs) | 2011-02-28 | 2015-09-30 | Ústav organické chemie a biochemie, Akademie věd ČR v. v. i. | Pyrimidinové sloučeniny inhibující tvorbu oxidu dusnatého a prostaglandinu E2, způsob výroby a použití |
| US20150152114A1 (en) * | 2012-08-06 | 2015-06-04 | Enantia, S.L. | Process for the preparation of an intermediate for a triazolopyrimidine carbonucleoside |
| CN103936681B (zh) * | 2014-04-04 | 2015-07-29 | 苏州开元民生科技股份有限公司 | 2-氨基-4,6-二氯-5-甲酰胺基嘧啶的制备方法 |
| CN115536595B (zh) * | 2022-11-29 | 2023-03-10 | 苏州开元民生科技股份有限公司 | 一种2-氨基-4,6-二氯-5-甲酰胺基嘧啶的合成方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4627872A (en) * | 1984-12-12 | 1986-12-09 | Bayer Aktiengesellschaft | 2,4-diaminopyrimidines |
| US5011927A (en) * | 1989-01-10 | 1991-04-30 | Basf Aktiengesellschaft | Preparation of 2-amino-4-fluoropyrimidine derivatives |
| US5294710A (en) * | 1992-01-22 | 1994-03-15 | Lonza Ltd. | N-5-protected 2,5-diamino-4,6-dichloropyrimidines and process for their production |
| KR950032143A (ko) * | 1994-04-27 | 1995-12-20 | 한스 피터 피르터, 토마스 케플러 | N-(2-아미노-4,6-디클로로피리미딘-5-일)포름아미드 및 그의 제조방법 |
| KR950032139A (ko) * | 1994-05-13 | 1995-12-20 | 빌헬름 도브라미슬·알프레트 노이바우어 | 2-아미노-4,6-디클로로피리미딘의 제조방법 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4965270A (en) * | 1987-05-30 | 1990-10-23 | Beecham Group P.L.C. | Purine derivatives |
| CN1019575B (zh) * | 1988-02-19 | 1992-12-23 | 石原产业株式会社 | 2-氨基-4，6-二氯嘧啶的生产方法 |
| GB8916698D0 (en) * | 1989-07-21 | 1989-09-06 | Beecham Group Plc | Novel process |
| GB9402161D0 (en) * | 1994-02-04 | 1994-03-30 | Wellcome Found | Chloropyrimidine intermediates |
-
1999
- 1999-12-15 DK DK99125042T patent/DK1013647T3/da active
- 1999-12-15 EP EP99125042A patent/EP1013647B1/de not_active Expired - Lifetime
- 1999-12-15 DE DE59903535T patent/DE59903535D1/de not_active Expired - Fee Related
- 1999-12-15 DE DE59907401T patent/DE59907401D1/de not_active Expired - Fee Related
- 1999-12-15 ES ES01130001T patent/ES2204798T3/es not_active Expired - Lifetime
- 1999-12-15 AT AT01130001T patent/ATE252087T1/de not_active IP Right Cessation
- 1999-12-15 AT AT99125042T patent/ATE228508T1/de not_active IP Right Cessation
- 1999-12-15 PT PT99125042T patent/PT1013647E/pt unknown
- 1999-12-15 EP EP01130001A patent/EP1188750B1/de not_active Expired - Lifetime
- 1999-12-15 ES ES99125042T patent/ES2187112T3/es not_active Expired - Lifetime
- 1999-12-16 HU HU9904608A patent/HUP9904608A3/hu unknown
- 1999-12-16 US US09/461,244 patent/US6271376B1/en not_active Expired - Fee Related
- 1999-12-16 SK SK1784-99A patent/SK283681B6/sk not_active IP Right Cessation
- 1999-12-16 SK SK683-2003A patent/SK285222B6/sk not_active IP Right Cessation
- 1999-12-17 CZ CZ0459899A patent/CZ296753B6/cs not_active IP Right Cessation
- 1999-12-17 CN CNB991262441A patent/CN1156449C/zh not_active Expired - Fee Related
- 1999-12-17 JP JP35977899A patent/JP3543709B2/ja not_active Expired - Fee Related
- 1999-12-17 CZ CZ20050024A patent/CZ296832B6/cs not_active IP Right Cessation
- 1999-12-20 NO NO19996325A patent/NO313878B1/no not_active IP Right Cessation
- 1999-12-21 PL PL99337354A patent/PL337354A1/xx not_active IP Right Cessation
- 1999-12-21 CA CA002293011A patent/CA2293011C/en not_active Expired - Fee Related
- 1999-12-21 KR KR1019990059846A patent/KR100645270B1/ko not_active IP Right Cessation
-
2001
- 2001-05-31 US US09/867,552 patent/US6716981B2/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4627872A (en) * | 1984-12-12 | 1986-12-09 | Bayer Aktiengesellschaft | 2,4-diaminopyrimidines |
| US5011927A (en) * | 1989-01-10 | 1991-04-30 | Basf Aktiengesellschaft | Preparation of 2-amino-4-fluoropyrimidine derivatives |
| US5294710A (en) * | 1992-01-22 | 1994-03-15 | Lonza Ltd. | N-5-protected 2,5-diamino-4,6-dichloropyrimidines and process for their production |
| KR950032143A (ko) * | 1994-04-27 | 1995-12-20 | 한스 피터 피르터, 토마스 케플러 | N-(2-아미노-4,6-디클로로피리미딘-5-일)포름아미드 및 그의 제조방법 |
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